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Issue 9, 2016
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Approach to the synthesis of the C1–C11 and C14–C18 portion of Leucascandrolide A

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Abstract

An asymmetric synthesis of the C1 to C11 and C14 to C18 fragments of the macrocyclic portion of the antibiotic Leucascandrolide A was achieved in 21 total steps from an achiral dienoate. The key 4-hydroxy-2,5-pyran portion of the natural product was established by oxy-Michael cyclization of a 5,7,9,11-tetraol intermediate, which in turn was established by an iterative asymmetric-hydration of dienoates. Alternative strategies for establishing the polyol stereochemistry were explored.

Graphical abstract: Approach to the synthesis of the C1–C11 and C14–C18 portion of Leucascandrolide A

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Supplementary files

Article information


Submitted
20 Jun 2016
Accepted
12 Jul 2016
First published
12 Jul 2016

Org. Chem. Front., 2016,3, 1120-1125
Article type
Research Article
Author version available

Approach to the synthesis of the C1–C11 and C14–C18 portion of Leucascandrolide A

T. J. Hunter, J. Zheng and G. A. O'Doherty, Org. Chem. Front., 2016, 3, 1120 DOI: 10.1039/C6QO00284F

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